|Minimum Stay||7 nights|
Windwardside Guest Cottage is the smallest of the Calabash Cottages group but our guests love it. Our goal in constructing Windwardside Guest Cottage was to provide a romantic haven packed with amenities but at a reasonable price. We have many honeymoon guests that choose Windwardside Guest Cottage for precisely this reason It is a budget home that won’t make you feel like you have made any compromises. But the cottage is not only for honeymoon couples- it is a quaint and lovely cottage for any visitors to the island that want an intimate experience of our beautiful island with a gorgeous view.
IMPORTANT INFO ABOUT RATES AND POLICIES: Our rental week runs from Sunday to Sunday. We have two rates: Low season from April 16 to December 14 and High season from December 15 to April 15. The rates are as listed. The only additional charge is 12.5% hotel tax. We do not collect a damage deposit. Our 20 year relationship with guests has taught us that this is not necessary. We treat our guests with respect and we have found that they return the favor. There are no extra costs for reservations, cleaning or service. If you encounter any additional charges when requesting a detailed quote it would be from the advertising site where you found us. Calabash Cottages is an established company and information about our rentals is easily found..
Car Rentals: Since the purchase of Homeaway and VRBO by Expedia we have seen an attachment at the bottom of our ads with them encouraging guests to book car rentals through their site. Because of our unique location we strongly advise against that. You do need a 4 wheel drive vehicle. We have for over 20 years done business with a very reliable company, Courtesy Car Rental. We believe in them enough that we forgo the commission they would give us and to apply it as a discount to your car rental. Please discuss car rentals with us before reserving. Our most important interest is in satisfying our customers. But the recent take over of our advertising sites by large corporations is constructing communication barriers. We can always be contacted directly.
We have numerous storage areas in a compact home with a a view that rivals any on the island. At Windwardside Guest Cottage you will wake up in a four poster bed to a gorgeous view of the Caribbean sea framed by palm trees. You could easily create a post card from the view of this adorable cottage.
The interior has a queen-size, four-poster bed, a small seating area, a kitchenette and a breakfast bar. The furnishings are both tasteful and cheerful. The covered porch has a dining area and two lounging chairs where you can enjoy the trade winds or good book while watching the sailboats pass by. A small gas grill is also available if you prefer to prepare your meals over looking the sea. A shower garden opens onto an uncovered deck. There you can have a relaxing evening soak in the hot tub under a starry Caribbean sky. The hot tub also has a wide view of the sea and total privacy.
In short Windwardside Guest Cottage offers a serene location, fabulous view, charming furnishings, a private hot tub, kitchenette and bbq, plus the dedicated staff of Calabash Cottages who will organize your vacation from start to finish all for the price of a hotel room. We provide snorkel gear, beach chairs and a cooler and a beach umbrella
We also include amenities that you may never need on our casual island (including an iron and a blow dryer) because we want you to be able to travel as light and carefree as possible. Please read reviews from out former guests. We hope to host you on our next visit to St. John.
We are thirty year residents of St. John. My husband is a retired builder and we designed this home together. We built Windwardside in 1996 and have managed it as part of the Calabash Cottages group for over 20 years. Calabash Cottages offers charming and private cottages and villas in quiet secluded locations. Our main focus is to provide an assortment of options for couples in a tranquil setting.
We and our staff always do our best to insure your precious vacation time is well spent at one of our Calabash Cottages. We are very happy to answer any questions to help you decide if Windwardside Guest Cottage or one of our other Calabash Cottages is a good fit for you.
Susan Brierley purchased this cottage in 1996
We love Coral Bay and wanted to design a home that did not tower over the hillside but fit into it's natural surroundings. The shape and orientation allowed of this property allowed us to do just that while still offering fabulous views. We love quiet natural settings, tropical gardens and ocean views and we appeal to visitors who are looking for just that.
Windwardside Guest Cottage will make you fall in love with the view from the front porch. The first thing you will see in the morning right from your four poster bed is the palm fronds waving in the breeze. This compact cottage offers many amenities. It is also a great choice for two couples when rented with Windwardside Main House as each has a lot of privacy.
Despite the picturesque setting, this villa was a romance killer in the heat of early June. There were no trade winds, just sticky, still heat. Just a little bit of air conditioning could have changed everything.
It was a very long ride from the airport with many winding roads. The villa is just as small as it looks and the kitchen is too small to cook in and there is only a dorm fridge and stovetop, no oven. Also no washer/dryer. In the bathroom, there was only antibacterial soap, no shower gel, shampoo or conditioner. I would not consider this villa well appointed as it is missing quite a few comforts of home.
There was a power outage which killed the only source of breeze, the fan and also no water.
My husband and I spent each day getting out as early as we could and taking in the many beautiful beaches the island offered. We stayed out as long as we could because we did not want to go back to the hot villa. It was hard to sleep, we were hot and sticky and this did not make for a very romantic setting.
Many of the beaches offer no amenities whatsoever, you must pack an ice chest with food and drinks and bring chairs (which were provided with villa). If a relaxing vacation with food and drinks on the beach is what you have in mind, this really is not the place to go. I realize that the trade-off for having no development on the beaches is the natural scenery, but we went to Grand Cayman later in the summer with our family and that is the kind of island vacation we like...air conditioners, full kitchens in the condo which is on the beach footsteps away from the water and cold drinks abound.
We ended up leaving a day early because that was the soonest we could get out with making a flight change. We have no interest in going back to St. John.
The owner did offer us use of the larger home nextdoor with a full kitchen, etc. but we did not find it to be any cooler over there. She also was able to give us a partial refund for the unused time of the rental car, but nothing on the villa.
For the first time ever, my husband and I decided to vacation in the same place 2 years in a row:Windward Side Cottage in St John. We had such a fairytale perfect time there last year, we knew any other place would probably disappoint in comparison. And Windward Side cottage was every bit as clean, romantic, well-appointed, fun, and comfortable as last year. Susan and her staff think of everything and see to every detail. To wake every morning and see the sunrise and gorgeous view right from your bed, to spend the day face-down in the beautiful calm clear waters of Salt Pond Bay and other great snorkeling beaches around Coral Bay, to spend time chatting with total strangers on this friendly island, to be surprised by baby donkeys and goats around every twisty turn of the road, and to get to love the hair-raising drive up the mountain...all make us miss this beautiful place.
Our experience with the Calabash Cottage staff could not have been better, they took care of every detail! We had a wonderful trip and plan to return some day soon. We will most definitely do business with this rental company again. Thanks for everything!
Perfect place for a 2 person getaway! All the staff made planning and everything on travel days go really smooth and stress free--arranging taxis, rental cars, and generally having good advice. The house itself was great, very small but has everything you need. The views from the cottage are amazing. The hot tub was great, we used it every night! The drive up from the main road to the cottage is pretty intimidating, but went well after the first time. Close to quite a few good restaurants on that side of the island. If you cook, make sure to clean the dishes right away and get up any crumbs, as the ants will find their way in quickly (but if you clean well won't be a problem). Also loved the outdoor shower!
The cottage was absolutely a paradise. It was tiny but clean and maintained down to the smallest detail. Breakfasts on the balcony with the stunning view will we never forget.
We have never been so welcomed and taken cared off. The whole arrangement with taxis, pickup and car rental was excellent.
We will be back!!! Thanks for everything!!!
This cottage was all we expected from the exciting pictures on the web. It did not disappoint. The view was even better than expected. Everything was clean and well organized, with many extras helpfully available. The location on the quiet side of the island a dream, with excellent restaurants nearby.
The transportation from the St. Thomas airport to the St. John ferry and back, the car rental, a leisurely stop at the one big supermarket, and the taking us to the cottage upon arrival were all arranged for us as promised. The greeter was terrific! She guided us through all this with patience and many suggestions and information that proved very helpful later.
The car rental agency that was arranged was also helpful, letting us park there when visiting Cruz Bay and even taking us back to the ferry at the end when he saw how much luggage we had.
Four wheel drive is necessary to get to the cottage (Mr. Toad's wild ride up the mountain on dirt roads), but the view and quiet are well worth it (just toads at night, roosters in the morning, and stars overhead.) And four wheel drive (the island is awash in Jeeps) is necessary to get to the great isolated beach at Little Lameshur Bay for swimming and snorkeling.
They promised a 5 star vacation, and it was! Thanks to all.
Remote and quiet setting, three quarters of a mile up dirt road with very little traffic. Beautiful view of Coral Bay and nearby islands. Near to beaches, shops restaurants, hiking trails and boating. Shares no facilities with other home on property except parking area.
There is an additional 12.5% hotel tax that will be added to the weekly rate.
12/15 - 4/15 $1610/weekly (2 Guests).
4/16 - 12/14 $1330/weekly (2 Guests).
Hotel tax in the Virgin Islands is increasing to 12.5% as of January 1, 2016.
For larger groups the guest cottage can be rented along with the neighboring Windwardside Main House.
For that option, or to see our other cottage for two, Sago Cottage, please see our additional listings on the St. John page.
Check or money order. 50% at time of reservation. Balance due 30 days before arrival.